The easiest team i have played is Southampton in League 1. despite having a 10 point deduction at the start, you have a bit of cash, and some quality young players (schneiderlin and lallana for example). Then, if you have the latest update, the chairman keeps dropping in with the spare change he found behind the sofa - usually in the 10s of millions of £.
promoted first season from league 1 (thanks to a dramatic late run), and then straight up from the championship to the epl (not quite so dramatic). I just won the epl in 2013 with...
..................................Joe Hart
Kyle Naughton...Gary Cahill...Miles Addison...Ivan Obradovic
..............................Darron Gibson
...........Albin Ekdal...Jamie O'Hara...Febian Delph
...................Yannis Tafer...Romelu Lukaku
subs - Niclas Bentner, Sam Vokes, Daniele Galloppa, Owen Hargreaves, Sean Morrison, Daniele Di Matteo (gen), Jason Steele
One of the hardest games i've had was with Darlington in League 2